35865-33-9

35865-33-9 structure
35865-33-9 structure
  • Name: Dianemycin
  • Chemical Name: (E)-8-[7-hydroxy-2-[2-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-(5-methoxy-6-methyloxan-2-yl)oxy-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoic acid
  • CAS Number: 35865-33-9
  • Molecular Formula: C47H78O14
  • Molecular Weight: 867.11
  • Catalog: Signaling Pathways Anti-infection Bacterial
  • Create Date: 2017-07-19 15:10:45
  • Modify Date: 2024-01-29 22:34:55
  • Dianemycin (Nanchangmycin free base), produced by Streptomyces nanchangensis NS3226, inhibits gram-positive bacteria[1]. Dianemycin is a broad spectrum antiviral active against Zika virus[2].

Name (E)-8-[7-hydroxy-2-[2-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-(5-methoxy-6-methyloxan-2-yl)oxy-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoic acid
Synonyms Dianemycin
Description Dianemycin (Nanchangmycin free base), produced by Streptomyces nanchangensis NS3226, inhibits gram-positive bacteria[1]. Dianemycin is a broad spectrum antiviral active against Zika virus[2].
Related Catalog
Target

Bacteria[1] Zika virus[2]

In Vitro Dianemycin (Nanchangmycin) can be used as a growth promotant in poultry and to cure coccidiosis in chickens. Dianemycin is active against drug resistant strains of malaria[1]. Dianemycin (Nanchangmycin) as a potent inhibitor of Zika virus (ZIKV) entry across all cell types tested including physiologically relevant primary cells. Dianemycin potently reduces infection of all three strains of ZIKV across all three cell types. The IC50s for infection are between 0.1 and 0.4 μM while Dianemycin has low toxicity in these ranges. In addition, DENV is inhibited by Dianemycin across cell types[2].
References

[1]. Liu T, et al. Mechanism of thioesterase-catalyzed chain release in the biosynthesis of the polyether antibiotic Nanchangmycin. Chem Biol. 2008 May;15(5):449-58.

[2]. Rausch K, et al. Screening Bioactives Reveals Nanchangmycin as a Broad Spectrum Antiviral Active against Zika Virus. Cell Rep. 2017 Jan 17;18(3):804-815.

Density 1.21g/cm3
Boiling Point 910.3ºC at 760mmHg
Molecular Formula C47H78O14
Molecular Weight 867.11
Flash Point 256.4ºC
Exact Mass 866.53900
PSA 188.90000
LogP 6.14960
Index of Refraction 1.549

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HL5521000
CHEMICAL NAME :
Dianemycin
CAS REGISTRY NUMBER :
35865-33-9
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C47-H78-O14
MOLECULAR WEIGHT :
867.25
WISWESSER LINE NOTATION :
T6OXTJ DQ E1 FY1&1UY1&VY1&1Y1&VQ B-& BT5OXTJ E1 E- ET6OXTJ C1 DO- FT6OTJ B1 CO1& B-& BT5OXTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
150 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
37ASAA "Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Grayson, M., and D. Eckroth, eds., New York, John Wiley & Sons, Inc., 1978 Volume(issue)/page/year: 3,47,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
9 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
37ASAA "Kirk-Othmer Encyclopedia of Chemical Technology," 3rd ed., Grayson, M., and D. Eckroth, eds., New York, John Wiley & Sons, Inc., 1978 Volume(issue)/page/year: 3,47,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 22,161,1969
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